


Babysitting Can Be Educational

by SolumSam



Category: Supernatural
Genre: Age Difference, Anal Fingering, Anal Sex, Babysitter AU, Babysitting, Barebacking, Bottom Castiel, Bottom!Cas, Cas has a headache, Comforting Dean, Crying, Experienced Dean, Experienced!Dean, First Time, Fluff, Friends to Lovers, Kissing, M/M, Massage, Massaging, Older!Dean, Praise Kink, Smut, Top Dean, Twink!Cas, Virgin Castiel, all that fun stuff, kind of a praise kink??, neck biting, neck kisses, nod nod, they're home alone, top!dean, virgin!cas, wink wink
Language: English
Status: Completed
Published: 2016-04-27
Updated: 2016-04-27
Packaged: 2018-06-04 19:24:52
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,224
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6672439
Author URL: https://archiveofourown.org/users/SolumSam/pseuds/SolumSam
Summary: <blockquote class="userstuff">
              <p>Castiel hates being babysat. It makes him feel like a child.<br/>But when it's Dean Winchester, he's more than okay with it.</p>
            </blockquote>





	Babysitting Can Be Educational

Babysitter.

Castiel hated that word. It made him feel childish, like he was still in kindergarten and didn't know how to dress himself. But the fact that it was Dean made him feel a little better. Dean was older - he attended college and had a job and a car and expensive glasses and dress shirts. He walked around with his shoulders back and a serious look written on his face. For some people it might have looked as if he were rude, but Cas knew the real Dean. The one who let him stay up later than his scheduled bedtime - the one who let him have a cookie in the cookie jar. He liked Dean. Dean was cool.

"Alright, Cas, I'll be back by ten!" Naomi called as she threw a scarf around her neck. "Dean will be here any minute. I'll see you then!" She waved, then closed the door, leaving Castiel all by himself. 

It wasn't like he cared she went out so much. Ever since the divorce she made sure she kept herself occupied - whether that was going to a movie with friends or on a date with a new man. But it didn't matter. It didn't bother him. She was having fun. 

He sighed, rubbing at his temples. That familiar ache had started, and he mentally cursed, making his way to the kitchen. A few lights were on, and he shut them off, the room now nearly completely dark, other than the natural light shining in from the windows. Hopefully the headache would stop by the time Dean arrived. Cas hated when Dean was there for his migraines. They were embarrassing, for some reason. He didn't really know why. Probably because he already felt so childish for needing a sitter at the age of fourteen, and when he sat in his room, whimpering at the pain, he felt even more like a baby.

A knock sounded. Castiel winced slightly, keeping his eyes closed as he made his way to the front door. When he opened it, Dean was there as expected, standing in a pair of dark jeans and a white button-up shirt. He grinned. "Hey, Cas," he greeted, adjusting his square glasses (which made him look older than nineteen). Cas managed a smile, then felt the jabbing pain once more, and flinched. "Fuck," he muttered, trying to control his breathing. "'M sorry, Dean," he said a little louder. "My head, it's - "

Dean gave a concerned look, and walked inside as Cas moved back. "It's okay, it's okay," he said in a quieter voice. "We can go to your room for a bit. Sound good?" Cas nodded grimly, and Dean closed the door behind them. As they walked upstairs, each step Castiel took, the throbbing pain in his head felt more intense. He tried to hide his whine, but Dean definitely heard it, because his hand was suddenly at his lower back, guiding him the rest of the way. "Hey, hey, it's alright," he soothed. "Let's go sit down." Dean led him to his room, settling on his bed across from him. The room was completely dark, and Cas was grateful. "I'll just be right here."

Several moments passed. Abruptly his head began to pound even more, and he whimpered loudly. Dean stood and climbed on the bed, kneeling behind Cas. His large hands rested on his shoulders, and his thumbs made their way up to his neck, and he began rubbing gently. Cas tensed. "Shhhh," Dean whispered, digging his fingers in the tight muscles. 

Minutes passed, and soon, the headache started to fade away, much faster than it ever had before. Cas sighed, almost happily. 

"Is it gone?" Dean asked hopefully. 

Castiel nodded. "Not completely. But it feels much better."

Dean let his hands off of his neck, and made his way off the bed. Dean figured he would start to go downstairs, but to his surprise, Dean kneeled in front of him.  


"What - "

Before Cas could say anything else, Dean's hands were on his face, massaging his jaw, then his temples. Cas tried to contain his moan, but failed miserably, and Dean chuckled. "You like that, Cas?"

Castiel nodded against him.

A brief moment of comfortable silence filled the air. Then Dean stopped rubbing, sliding his hands down his face and cupping his jaw. Cas opened his eyes, not even realizing he'd closed them, and noticed how close Dean was to him. It was dark, but his eyes had adjusted, and he saw Dean's large eyes gazing up on him.  


"Have I ever told you," Dean said, "how beautiful you are?" He caressed his bottom lip with his thumb, and Cas's breath hitched in his throat.

"I - I - "  


Dean moved in closer. "Is this okay, Cas?" he whispered.

Castiel could smell his breath - a mixture between sweet apples and fresh mint. Dean's lips were so close to his own. "Y-y-yes," he stuttered, staring into his eyes.  


Dean closed the space between them, slowly. The way their lips brushed was tender. It was sweet. Cas had only kissed one other person in his whole life, and that had been in the fourth grade. It felt strange, having another pair of lips on his own. But they were soft and warm and all he could think about was how right it felt. Dean deepened the kiss - only slightly - but he could feel his tongue press gently at his lips. Cas opened, allowing entrance, and when Dean's tongue explored his mouth, he gasped. It was wet and smooth and besides the fact that Cas was incredibly inexperienced, it felt wonderful regardless. 

It may have been only seconds, or minutes - Cas didn't know, but he felt Dean's hands come off his face and slide down to his thigh, squeezing, almost asking. In response Cas wound his arms around Dean's neck, deepening the kiss even more, and Dean moaned, making Cas shudder. His hands went further, until they were pressing against Castiel's forming erection. He gasped into Dean's mouth, and Dean pulled away, pressing kisses down to his jaw. Cas whimpered. 

Soon, he could feel Dean standing, grabbing Castiel and gently setting him on his back against the bed. Dean hovered over him, his arms on either side, and continued with the wet kisses against his neck. His hand ground into his erection, and Cas reached up to grab Dean, squeezing whenever Dean sucked at the right spot.  


He'd never felt this before. He was a virgin, he'd never been touched like this from anyone else but himself. 

His dick was throbbing underneath them, and Dean released his mouth from Cas's wet collarbone. His skilled hands undid Castiel's belt, then grabbed the loops and pulled them all the way down to his knees. Cas was uncomfortably hard - his underwear was now wet and he panted heavily when Dean peppered wet kisses down his stomach. When his mouth was right next to Castiel's dick, he made no hesitation when he mouthed at it and sucked gently through the cotton. Cas writhed underneath him, gripping his bed sheets and crying out. "J-Jesus C-C-Christ," he cursed, trying to control himself.

Dean stopped, sitting back and taking off his glasses, setting them on the nightstand beside them. Then he hooked his fingers in his underwear, pulling them down slowly. A low growl was heard from him when he laid eyes on Cas's dick. Typically, Cas would be embarrassed by it, and would shy away. But his arousal was so high he didn't even care. 

"Spread your legs for me, baby," Dean whispered, settling his hands on both of his thighs.

Cas did as told, his heavy breathing the only sound in the room. Dean reached in his back pocket and pulled out his wallet. 

"What - " Castiel was about to ask what he was doing, but then he saw a small bottle of clear liquid in Dean's hands. "Oh," he said dumbly, realization hitting him hard. That was lube. Dean was going to fuck him. Oh, my God. Dean was going to be inside of him. 

"Is that okay?" Dean began taking off his own clothes, starting first with his shirt, and then his pants. 

Castiel's eyes caught onto Dean's toned torso, and he tried to control his breathing. Fuck. It was more than okay. He made eye contact with him, and nodded, probably more intensely than he needed to. Dean breathed a laugh, then continued to fumble with his own belt. Cas's gaze was glued onto Dean's shaky hands, and he was taken aback. Was Dean nervous too? A pleased feeling struck in him. Maybe he wasn't the only one who felt awkward. 

As Dean's pants came off, so did his underwear, and when Cas saw his cock, he swallowed. Holy fuck. He was huge. Dean leaned in, balancing on his elbows as his nose trailed up to his neck and finally paused at his ear. "Don't worry, it'll fit," he whispered, and Cas's breath hitched in his throat. He pulled away, then opened the bottle of lube, rubbing some on his fingers. "Are you ready?" he asked.

Cas took a deep breath, and tried to calm his struck nerves. "Y-yes," he responded, swallowing. "Just - just go slow." 

Dean nodded. "Of course, baby," he said, then leaned back down to Cas's ear. "I'm going to start now."

Cas nodded, and waited. 

His finger rubbed against the entrance, and Cas breathed out a shaky breath. He slowly began pushing it in, his hot breath against Cas's ear. When it was fully in, Cas clenched unconsiously. Dean tried to move around, but the muscle was tight. "Cas, baby, you gotta relax," he said, giving a gentle kiss below his ear. Cas's breathing quickened, and he gripped at Dean's shoulders. "Hey, hey, baby," he soothed, pressing several kisses down his neck. "You're okay. Relax. Relax. I'm gonna make you feel so good." 

Cas nodded, closing his eyes and swallowing hard. Slowly, he unclenched around Dean's finger, and let out a deep breath through his nose. "K-keep going," he rasped, his fingers loosening their grip on Dean's shoulder. 

Dean started to move the finger around inside of him, slowly, and Cas fought to keep himself calm. It didn't hurt, but it felt strange. When he was stretched a little more, Dean kissed his neck again. "I'm going to put another in, okay?" he asked, and Cas nodded quickly. "I'll be careful, I promise."

Then, deliberately, a second was added. Cas tried to not clench, but he couldn't help it. "S-sorry, sorry, sorry," he whimpered, breathing heavily. 

Dean peppered kisses along his neck and across his face, all the way to his lips. "Baby, it's okay," he replied quietly, his fingers still. "Take your time. You're fine, baby. You're so good for me." 

Moments passed. Cas finally relaxed, the fingers inside him suddenly feeling much more comfortable. Dean seemed to notice, and put them in a little deeper, crooking them to the right. 

And oh my God did it hit something.

"F-fuck!" Cas screamed in pleasure, scratching Dean's shoulders. "Fuck!"

Dean chuckled, kissing him everywhere, even his eyelids. "Feel good, baby?"

Cas noticed his rapid breathing and tried to calm himself down. But shit, that really got him going. His dick twitched in interest, and he moaned at the thought of Dean ramming himself into that certain place. "Fuck," he whispered under his breath. "Another, please!" 

Dean laughed breathily, then pressed a third finger inside him. It didn't feel as bad this time, although there was that slow burn still. Dean scissored his fingers inside him, then pushed them deeper, hitting that spot again. Cas cried out.

"Fuck, Dean! Hurry!" 

Dean groaned against his neck, grinding his dick against Castiel's thigh. "Want you so bad, Cas," he whined. "You're so tight. So fucking tight. Are you ready for me, baby?" 

Cas whimpered and nodded. 

Dean reached down and grabbed his wallet, rumaging through it hungrily. "Fuck," he cursed, throwing it down on the ground. "I don't have a fucking condom."  


Cas's heart sank. Did that mean they couldn't -

"Is it okay if we do it bareback?" Dean stared at him with hopeful, wide eyes.

The younger boy nodded. "Y-yeah," he said. He wanted to do this. He wanted to do it so fucking bad, with or without the stupid rubber.

Dean grabbed the bottle of lube and slathered a generous amount on his rock-hard dick, then rubbed some into Cas's hole, making him hiss in surprise. Dean chuckled, then nabbed a pillow from the bed. "I'm gonna put this underneath your hips, okay? It'll make it easier."

Cas nodded and lifted himself up, letting his lower back rest against the nice, fluffed pillow. 

"Okay, I'm going in now," Dean whispered, lowering himself to kiss the boy beneath him. "Tell me if it's hurting, okay, baby?"

Cas nodded once more, then wrapped his legs around Dean's lowerback, relaxing himself as much as possible. It'll feel good. It'll feel fucking amazing, because this was Dean Winchester. He'd make sure it was pleasurable for the both of them. 

The head of his dick pressed against Castiel's hole, then pushed in a little more, causing Cas to reach up and wrap his arms around Dean's back. Dean lowered himself even more, peppering kisses along his neck. Cas sucked in a sharp breath when he pushed further. 

"God, you're doing so well for me, baby boy," he commented, panting heavily. "You feel so good. So nice and tight." 

It hurt. It fucking hurt. It ached and it burned but he didn't want to say anything. He couldn't let Dean down. He couldn't. Tears threatened to spill, but he blinked them away. Crying right now would be so embarrassing. 

When Dean bottomed out, Cas felt incredibly full. 

"Damnit, Cas," Dean whispered hoarsely. "You're so tight and warm. Just for me." When Cas didn't reply, Dean lifted his head up, staring at him worriedly. "Cas? Are you okay?" 

Cas swallowed, his breath shaky and uneven. "Y-you're big," he admitted, trying to relax himself.

The older boy gave a concerned smile. "Yeah," he agreed, then kissed him on the side of his mouth. "But you're doing amazing, baby. So good for me. Tell me when I can move, alright?"

After several moments of waiting, Castiel finally took a deep breath and nodded. "You can move now," he told him.

"Are you sure?" Dean questioned.

Cas nodded once more. "Yes."

Dean seemed to hesitate, but kissed him and nodded as well. "Okay, baby. I'll go slow." He dipped his head into the crevice of Cas's neck, his warm breath creating goosebumps on his bare skin. Then he pulled out slowly, making Cas's hole to clench in reflex. "Relax, baby," he said, feeling him tense. "It'll feel better if you're relaxed."

Cas nodded. 

Then he pushed back in, thrusting his hips and creating a nice rhthym. Cas squeezed onto his back, panting unevenly and whining when Dean got a little faster. Abruptly, when Dean thrust back in, he hit a spot inside him that caused him to cry out. "God," he whimpered, feeling the pleasure rolling over him. "God."

Dean sucked softly at his neck, his warm tongue darting along his salty skin. In each thrust he hit his sweet spot, moaning when Cas clenched around him. Then he pressed kisses along his jawline, all the way back to his mouth. "How're you doin', baby?" he asked breathlessly. 

Cas's voice caught in his throat. Jesus, don't cry, Castiel, he told himself, but tears were already forming. It just felt so goddamn nice. When he didn't say anything yet again, Dean looked at him with a concerned expression. 

"Cas?" He lifted his arms up, and wiped the tears from the younger boy's cheeks with the pads of his thumbs. "Do we need to stop?" 

"N-no!" he cried, his hands travelling down Dean's spine, causing him to shiver. "Please keep going. Faster."

Dean visibly swallowed, but followed his orders and quickened his thrusts. Castiel moaned, writhing against him in pleasure, feeling that hardened dick inside him.  


"Be feelin' this for weeks," Dean murmured into his ear, nibbling on the lobe. "Gonna be walkin' weird, just because - " Cas clenched down on him and he moaned loudly, increasing his pace brutally. "Because of m-me," he managed to say. "Fuck, Castiel."

Cas shivered at his full name, then turned to kiss Dean. He tasted like sin. "Oh, ohhhhh, ahhhhh," he whined against the thrusts. His tears were spilling carelessly against his cheeks. He whined loudly when Dean reached in between them, grasping Castiel's dick and stroking it at a brutal pace. "Fuuuuck!" he screamed, and Dean nibbled at his neck, biting it softly, marking Cas. "I'm close, I'm close, Dean, I'm close," he chanted, and Dean nodded against him. 

"I know baby, I know," he rasped. "Me too. Oh, God, me too."

Castiel clenched around him, reaching for his own cock once Dean let go of it and started jerking it steadily. Only a moment later Dean's thrusts stuttered, and he was spilling hot cum inside Cas, crying out in pleasure as he bucked his hips through his orgasm. 

Cas whimpered at the feeling, and then felt his own orgasm closing in. "Ohh, oh, oh," he panted, reaching down and fucking his own fist at a brutal pace. He couldn't believe Dean came before him. His face scrunched as he closed his eyes, the feeling of his orgasm suddenly intensely rolling through him. "Ohhhhh," he moaned, feeling the long ropes of cum splash against Dean's chest. He kept jacking himself, milking himself through it as Dean moaned. When it was over, he pulled out of him and rolled off, lying beside him. 

It was silent for a long time.

Cas wasn't really sure what to say. 

"Damn," Dean announced, breaking the silence. "Who knew babysitting could be educational."

Cas laughed, his voice still hoarse from being so loud. Suddenly, he turned over, facing the younger boy and staring at him with his impossibly green eyes. He reached out, then traced his thumb against Cas's tear-stained cheeks. "You're beautiful," he whispered, and Cas looked away awkwardly. 

"Thank you," he murmured, swallowing.

Dean kept staring for another moment or so, then hopped up out of his bed and went to the bathroom. 

Cas sighed, wiping the sweat away from his forehead. He just lost his virginity to Dean Winchester. Fuck. He'd never guessed that that would've happened.  


A little while later, Dean came back completely cleaned off with a cold. wet towel in his hands. He climbed back in bed, then started wiping off Castiel's stomach, then his forehead. Cas melted against his touch. "You were so amazing for me, Cas," he commented, the corners of his mouth turning up. "I liked that a lot."

Castiel smiled. "I did too, Dean."

Hours later, when Naomi returned, Castiel's sex hair was back to normal (which was, infact, already sex hair) and they both had their clothes on. Dean was reading a book on the couch and Castiel was at the kitchen table doing his homework.

"Castiel!" Naomi's voice echoed throughout the house. "I'm home!"

"In the kitchen," Cas called back.

Naomi came up behind her son, ruffling his hair. "You guys have fun?"

Dean locked eyes with Cas, breaking out into an embarrassing large grin. "We sure did, Ms. Novak."

**Author's Note:**

> Thanks for reading! This wasn't edited, but I hope it was decent anyways.  
> Leave comments/kudos if you can. They mean the whole world to me!  
> Have a good rest of your night/day, and make sure to check out my other works too!


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